A Shy Artist
by RainbowViking
Summary: GAY YAOI M/M TWO MEN HAVING SEX! What do people not get about this, if you don't like gay sex scenes, don't read this.


So I wanted to try out some new things, like a little kink, I guess. I read this prompt on tumblr about cockslut!Dean, and I can only every think about him rocking shy!cas's world(in a high school au). I hope you like it!

Dean was hanging out by the lockers, he didn't usually show up this early, or even on time for that matter, but his art teacher was on his ass about finishing a project on time. He loved art and everything, but he took everything too seriously for his teacher's taste, and always needed extra time to get it done. Not to mention Dead thought about everyone in that class, save a few, getting undressed for him. He went to an all boy school, so it was like being a kid in a candy store whenever he was horny. Al he had to do was find some testosterone pumped jock to drag him down to the locker room and work out that frustration from losing whatever big game they were in. Dean didn't really give two shits about sports here. There was always this one guy in his class that bugged him though. Castiel Novak.

Dean thought he was cute and all, but he was the nerdy teacher's pet type of guy, along with being incredibly quiet. Dean had resented him slightly for being able to get amazing works of art done on time. Castiel didn't really talk to anyone in class much for whatever reason. No one really knew his story. Dean was increasingly curious, as jealous of Castiel as he was, Dean knew he wanted to "get to know" this kid. They were both seniors, but that's all Dean knew about Castiel. Dean tried to make "accidental" eye contact, but Castiel almost never looked up from his work, unless it was to pay gratitude to the teacher's compliments. Dean had a system to seduce boys in this school, it started with eye contact, then he'd bump in to the in the hallway and smile a confident smirk. Boys could never resist his almost in describable green eyes. People seemed to get lost in them like a meadow, the only thing to snap them back to life was for Dean to bat his eyelashes. He'd apologize in the slightly gruff, sexy voice. After a while, someone would make the first move. Dean thought it was weird that this still worked, he had kind of developed a reputation for being the school slut, which he liked.

Dean tried his usual tactics, but when he bumped into Castiel, all Castiel did was apologize and walk away. He couldn't even look Dean in the eyes. Dean noticed a feeling of worry for the dark haired boy. Dean actually felt kind of bad that all he could think about was that voice. A voice that sounded like Castiel gargled sandpaper and gravel every morning. Dean figured he'd have to try at his in a more direct manner. He made his way to class, trying to figure out what to say.

The next day, before the bell rung, Dean looked all over the place for Castiel, gripping A hot cup of black coffee, loaded with sugar in one hand, and a large envelope in the other, containing his latest drawing. He eventually found the silent boy in one of the art rooms, alone. Dean figured this would be the perfect time to strike. As he walked in, Castiel looked over his shoulder at Dean, and gave a terrified look, and tried to cover parts of the drawing, but it was too big for the young man to cover. Dean looked at it and was shocked. Castiel had been working with charcoal, he had drawn a boy, standing in some empty space, wrapping two dark wings around his body, only barely covering the parts Dean loved to see. The angel boy had his arms over his shoulders, a sexy smile across a familiar face. Dean looked at it and noticed the angel was himself.

"Uh..." Dean tried to find the words to express what he felt. Even though Dean wasn't quite sure what he felt. It was like a mixture of shock and flattery, surprise and joy.

"This isn't what it looks like, um, please don't be mad!" Castiel said quickly, trying hard to dull the awkwardness of the situation.

"It's beautiful..." Dean finally responded.

"Well, yeah, it is you after all..." Castiel said in the hushed tone, half hoping Dean wouldn't hear.

Dean didn't know how to react. This was the first time someone had thought of him as beautiful, and not just a fuck toy. Dean loved being fucked by random guys, but he never knew how great it was to be called beautiful. "I have to go, I'll see you in fourth period." he said, after he realized Castiel looked like he was going to shrink into himself from the awkwardness.

Castiel took this as Dean feeling awkward and freaking out for a second, until Dean turned back around and said, "I really like it. Thanks a lot, Cas."

After class was over, Dean noticed how desperate Castiel was to avoid eye contact. He went over to Castiel and tried to strike up a conversation.

"I can't believe how good you are, Cas. The drawing is amazing..." he said.

"Um, thanks, Dean. Sorry for not asking you first, it's just..." Castiel tried to speak, but he couldn't find the words.

"Hey, how did you get my body so well? Have you been peeping through my window?" Dean tried to joke.

"Uh, no... You probably don't remember, but we had gym together sophomore year. You hated putting on your clothes until the last second, so I got a pretty good view..." Castiel said, trying to be bold, but horrified at what was coming out of his mouth.

"Oh, yeah! I forgot you were there... Sorry man."

"It's alright, people always tell me I just blend into the wallpaper most of the time. No one really notices me very often." Castiel said, solemnly.

Dean felt a small amount of pity for Castiel, he felt the urge to hug him, but abstained.

"Hey, since you're so good, would you mind helping me with the water coloring stuff, I can't really mix it very well." Dean said, hoping for an excuse to get closer.

"I don't have my stuff with me, it's all at home."

"How about I come over to your house?"

"Oh, um, I'm not sure if my dad would be okay with me having people over..." Castiel said, shyly.

"Well, he doesn't have to know." Dean said.

"Yeah, um, okay. He doesn't get off work until 7pm tonight, so if you want to swing by for a few minutes, I can show you."

"Great, see you soon, Cas" Dean said, almost purring the name as it slipped through his pillowy lips.

Castiel was a little nervous, he had heard stories about Dean Winchester in the halls, but he didn't like putting faith in rumors. Although, a part of him wanted to see if they were true, almost hoping they were...

Dean walked down the neighborhood, swaying his hips as he walked. He wore a pair of tight jeans, he loved the way they showed off his round ass, his muscular legs, and his good sized bulge. Dean checked the address of the houses, until he found Castiel's house. He saw there was no car in the driveway, so he walked up to the house. It was only 4:28, so Dean had a little time.

As he knocked on Castiel's front door, he could hear fairly loud music coming from the back of the house. To his surprise, Castiel showed up soon after he knocked. Castiel, held the door for Dean, and they made his way to Castiel's art room. His parents gave him a whole room to paint and sculpt in. Castiel bend over to grab his pints from the drawer, and Dean made note of Castiel's cute ass in mildly tight shorts. Dean waited for Castiel to grab some acrylic paint, which their art techer taught them to mix with water to make watercolor paint. Dean watched as the boy poured only three drops into the water.

"And that's how you do it." said Castiel, a little more open, now that he's in his element.

"You seem a bit more lively, Cas."

"Yeah, I don't do well in large groups. I'm not the biggest fan of people in general."

"Heh, I couldn't disagree more, I couldn't survive without the guys at school." Dean said, hinting at his love for cock.

"Yeah, I've heard you just love the guys." Castiel said, sarcastically.

"Oh, so my reputation is getting around now."

"So, do you really, you know...?" Cas asked

"Yeah, a lot. Some people say I'm the school slut, but I think sex is just fun. I mean it feels so good, why should I limit myself?"

"I wouldn't know." Castiel said.

"Wait, what?"

"I've never had sex before. So I wouldn't know what it's like. Porn makes it look interesting, thought..."

"So, you're a virgin?"

"I can do with out the criticism, Winchester." Castiel said, defensively.

"No, not making fun of you or anything, I just assumed people would be all over you, ya know?"

"Yeah, well, you kind of need to talk to people to talk about sex."

"Not always." Dean said, with a wink.

After a brief silence, Dean moved a little closer to Castiel. Castiel noticed, and blushed. He was extremely nervous. Dean leaned in for a kiss, and Castiel moved closer as well. As their lips met, Dean moved his hand over Castiel's thigh, rubbing a little higher every second, until he felt Castiel's stone-hard erection, it was almost sticking out of his shorts. They made their way across the hallway, into Castiel's room. They sat next to each other at the foot of the bed, coming back in for the kiss. Dean ran his fingers under the annoying piece of fabric, and felt the foreskin of Castiel's cock. Dean was shocked, it was rare to find a guy with an uncut cock. Dean started guiding Castiel on his back, and unbuttoned Castiel's shorts without breaking the kiss, and Castiels cock flopped out, smacking his stomach before sticking straight up. Dean ran a finger over the length of it, he figured it had to be a good seven inches. Castiel moaned into the kiss, his sensitivity was unlike anything Dean had seen before. Dean started rubbing the foreskin before pulling it back and jerking Castiel's cock. It only took about 4 pumps before Castiel shot his load everywhere. Dean licked his hand, tasting the cum, it was salty, but sweet. Castiel was panting slightly on the bed, his shorts around his ankles. Dean sat up and took off his shirt and wiped the cum off of Castiel.

Dean wasn't just satisfied by making him cum from a handjob, he wanted more, and from the way Castiel was getting hard again, he seemed to want more too. Dean was shocked by Castiel's vitality. He decided to help him get harder by sucking on the tip for a bit. His full lips wrapped around the head, sucking lightly as his head bobs up and down between the darker haired boy's legs. Dean started taking more and more in every time he came back down. Castiel was still getting a little bit of over stimulatoin, but he didn't care, he was in Dean Winchester's mouth. After Castiel was fully hard, Dean stood up.

"So, got any condoms?"

Castiel shook his head.

"Lube?"

Castiel reached up to the table by his bed and puled out a bottle of lube and tossed it to Dean. Castiel wan't sure who was going to be the bottom, he was nervous, but felt a wave of relief when Dean crawled over him and rubbed his hole against Castiel's cock.

"So, do you want to get me ready before we lube up?" Dean said, hinting to Castiel to tongue fuck him for a bit.

Dean rolled off of him and got on all fours, arching his back to make his round backside look even bigger. Castiel pulled Dean's shorts down, exposing a cute, flawless ass. Castiel started by kissing the cheeks, slowly. Rubbing them both before spreading them gently to reveal a fairly tight hole. Dean was shocked by the tenderness, the care. Guys usually just jammed their tongue in and spitting on the hole. Castiel gave a quick flick of his tongue over the hole before running it slowly over the rim. Dean moaned a little, a drop of precum sat on the tip of his dick. Castiel took this as a sign to move on, he darted his tongue back and forth, going in a little deeper every time, until he got half his tongue in. Castiel was proud of himself, 'I knew watching all that porn would pay off' he thought. After he pulled his tongue out, Castiel grabbed the lube from Dean's hand. Dean's face was bright red, and he was stroking his cock as more precum fell onto the blanket. Castiel put plenty of lube on his fingers and the loosened hole before pushing one in. Dean stroked his cock a little harder when he felt Castiel hit his prostate. Castiel kept pushing on the spot, rubbing in circles over it, before he pushed in the next finger.

After Castiel had three fingers in, he played with Dean's hot spot a bit more before he squeezed a spot on Dean's hips that made his shiver. Castiel pulled his fingers out and started rubbing lube onto his erect shaft. Dean had gotten up before Castiel could put his dick in, and pushed Castiel onto his back. Dean straddled Castiel's sizable cock before he pushed his ass down on it, sliding slowly down, until Castiel's cock was all the way in. Dean hadn't taken a cock in without a condom in a long time, he forgot what it felt like. The foreskin gave a new sensation as well. Dean moved up and down, while trying to keep his balance. Castiel noticed Dean struggling, so he cupped Dean's ass and tried to keep him steady. Which gave Dean more of a chance to rub his own manhood. After a while, Dean was bouncing on Castiel's cock faster, his own cock twitching every time he slammed his prostate against Castiel's cock.

Castiel grabbed Dean's hips and pulled him to a stop al the way down on his shaft.

"I want to get on top of you." Castiel said.

Dean complied and laid on his back, Castiel grabbed Dean's legs and Rested them on his shoulders, Castiel pushed his swollen shaft into Dean's not-so-tight-anymore hole, and started fucking him slowly. Castiel took his time, feeling every inch of Dean's ass. Castiel moved Dean's legs off his shoulder and around his waist before wrapping his arms around Dean, sliding in and out slowly, while holding Dean close. Dean felt so safe and calm, but letting go of the power made him feel vulnerable. Dean was okay with this anyway, he could feel that Castiel wouldn't hurt him. Castiel kissed every inch of Dean's neck, pumping his hips a little faster. Castiel started licking and biting Dean's neck. He bit gently, but licked over the spot every time, and gently kissed it if he thought he bit too hard. Castiel slowly worked up the pace, never letting go of Dean. Eventually, Dean was moaning Castiel's name.

"Cas, I'm ready to cum. I want you to finish inside me." Dean breathed into Castiel's ear.

Cas was close too, he held onto Dean as he came inside. Every shot brought a new wave of pleasure. After Dean felt Cas shooting in him, he started cumming too, this was the first time Dean came without touching himself. He shot so hard between Castiel's stomach and his own, Cas hadn't stopped thrusting slowly in and out of Dean. After a while, Castiel stopped, and they laid there, Dean still in Castiel's arms. They cuddled until they saw the clock. 6:49. Dean grabbed his clothes, threw on his shorts and kissed Castiel for what seemed like forever. By the time Dean stopped and ran out the door, it was 6:53. Cas just lay there under the covers.

Castiel's dad got home and called for Castiel. He threw on his shorts and walked out to greet him.

"Hey, dad. How was work?"

"It was fine. I saw this guy walking down the street. He was pretty cute, I think he was John Winchester's son. He seemed like a good fit for you, Castiel. You should ask him out. Maybe an outgoing guy like that can help you with your shyness." Mr. Novak said.

"Yeah, I think I'll ask him to dinner or something."


End file.
